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Mechanistic insights can resolve the low reactivity and selectivity issues in intermo-lecular Rauhut Currier (RC) reaction of γ-hydroxyenone

Abstract

Dimerization or isomerization of electron-deficient alkenes in presence of organophosphine catalysts comprise of the Rauhut Currier (RC) reaction. In this manuscript, we attempt to understand the reaction path and propose a mechanism based on evidence from computational simulations. The long-term goal is to establish the RC reaction as a general way of constructing complex natural products by dimerization. We used two selected substrates, dimethyl hydroxyacetone and hydroxyl pyrrolidinyl hydroxyacetone in the present study. The challenge to overcome is the lack of reactivity and selectivity. We found that the issue of low reactivity can be resolved by shifting the equilibrium of the enone/enolate forms of the substrate towards the enolate.

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Supplementary files

Article information


Submitted
30 May 2020
Accepted
27 Jun 2020
First published
29 Jun 2020

New J. Chem., 2020, Accepted Manuscript
Article type
Paper

Mechanistic insights can resolve the low reactivity and selectivity issues in intermo-lecular Rauhut Currier (RC) reaction of γ-hydroxyenone

Z. Ullah and R. Thomas, New J. Chem., 2020, Accepted Manuscript , DOI: 10.1039/D0NJ02732D

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